CN1093115C - 二羧酸结晶 - Google Patents
二羧酸结晶 Download PDFInfo
- Publication number
- CN1093115C CN1093115C CN98804115A CN98804115A CN1093115C CN 1093115 C CN1093115 C CN 1093115C CN 98804115 A CN98804115 A CN 98804115A CN 98804115 A CN98804115 A CN 98804115A CN 1093115 C CN1093115 C CN 1093115C
- Authority
- CN
- China
- Prior art keywords
- acid
- dicarboxylic acid
- anionic polymer
- crystallization
- molecular weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 238000002425 crystallisation Methods 0.000 claims abstract description 72
- 230000008025 crystallization Effects 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 63
- 239000002253 acid Substances 0.000 claims abstract description 20
- 229920006318 anionic polymer Polymers 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 1
- 229920001448 anionic polyelectrolyte Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 15
- 239000005518 polymer electrolyte Substances 0.000 description 15
- 125000000129 anionic group Chemical group 0.000 description 10
- 239000001361 adipic acid Substances 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 235000019580 granularity Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal cation Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000000280 densification Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19705329.7 | 1997-02-12 | ||
| DE19705329A DE19705329A1 (de) | 1997-02-12 | 1997-02-12 | Dicarbonsäurekristallisate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1252048A CN1252048A (zh) | 2000-05-03 |
| CN1093115C true CN1093115C (zh) | 2002-10-23 |
Family
ID=7820011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98804115A Expired - Fee Related CN1093115C (zh) | 1997-02-12 | 1998-02-09 | 二羧酸结晶 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6534680B1 (ja) |
| EP (1) | EP0968167B1 (ja) |
| JP (1) | JP3984297B2 (ja) |
| KR (1) | KR100509312B1 (ja) |
| CN (1) | CN1093115C (ja) |
| AU (1) | AU6296198A (ja) |
| BR (1) | BR9807326A (ja) |
| CA (1) | CA2280592A1 (ja) |
| DE (2) | DE19705329A1 (ja) |
| PL (1) | PL189983B1 (ja) |
| RU (1) | RU2195442C2 (ja) |
| UA (1) | UA54494C2 (ja) |
| WO (1) | WO1998035929A1 (ja) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2795720B1 (fr) * | 1999-06-29 | 2003-05-02 | Rhone Poulenc Fibres | Procede de cristallisation d'acide carboxylique et procede de fabrication d'acide carboxylique cristallise |
| TW460452B (en) * | 1998-09-14 | 2001-10-21 | Rhodia Fiber & Amp Resin Inter | Process for the crystallization of carboxylic acid and process for manufacturing crystalline carboxylic acid |
| FR2795721B1 (fr) | 1999-06-29 | 2003-04-18 | Rhone Poulenc Fibres | Procede de fabrication d'acide adipique |
| EP1198444A1 (en) * | 1999-07-23 | 2002-04-24 | Chemintel (India) Private Limited | Process for crystallization of dicarboxylic acids |
| JP2006321996A (ja) * | 2005-04-22 | 2006-11-30 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
| US20120021473A1 (en) * | 2010-04-01 | 2012-01-26 | Bioamber S.A.S. | Processes for producing carboxylic acids from fermentation broths containing their ammonium salts |
| EP2970082A1 (de) | 2013-03-15 | 2016-01-20 | Basf Se | Verfahren zur herstellung von rieselfähigen dicarbonsäure-kristallisaten |
| WO2016016375A1 (de) * | 2014-07-30 | 2016-02-04 | Basf Se | Verfahren zur herstellung von rieselfähigen und lagerstabilen dicarbonsäure-kristallen |
| FR3028864B1 (fr) * | 2014-11-26 | 2018-05-18 | Roquette Freres | Procede de recuperation de cristaux d'acide succinique avec mise en œuvre de tensioactifs au cours de la cristallisation, cristaux obtenus et leurs utilisations |
| CN108779088B (zh) | 2016-01-13 | 2021-10-08 | 斯道拉恩索公司 | 2,5-呋喃二甲酸及其中间体和衍生物的制备方法 |
| KR102341902B1 (ko) | 2016-09-09 | 2021-12-21 | 카오카부시키가이샤 | 디카르복실산 결정 및 그 제조 방법 |
| JP6944746B2 (ja) * | 2016-09-09 | 2021-10-06 | 花王株式会社 | ジカルボン酸結晶及びその製造方法 |
| WO2018230011A1 (ja) * | 2017-06-15 | 2018-12-20 | 花王株式会社 | ジカルボン酸結晶の製造方法 |
| JP7053220B2 (ja) * | 2017-06-15 | 2022-04-12 | 花王株式会社 | ジカルボン酸結晶の製造方法 |
| WO2019014393A1 (en) | 2017-07-12 | 2019-01-17 | Stora Enso Oyj | NOVEL PROCESSES FOR PREPARING 2,5-FURANDICARBOXYLIC ACID |
| AU2018301662B2 (en) | 2017-07-12 | 2022-06-30 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| JP7081946B2 (ja) * | 2018-03-13 | 2022-06-07 | 花王株式会社 | フマル酸結晶の製造方法 |
| CN113979860B (zh) * | 2021-11-11 | 2022-11-29 | 天津大学 | 一种2，4-二氯苯氧乙酸晶体及其制备方法和应用 |
| JP2023084097A (ja) * | 2021-12-06 | 2023-06-16 | 花王株式会社 | 芳香族ヒドロキシカルボン酸結晶の製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883640A (en) * | 1972-01-26 | 1975-05-13 | Ici Ltd | Sodium percarbonate crystals |
| US5296639A (en) * | 1992-12-18 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Adipic acid purification |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL273696A (ja) * | 1961-01-18 | |||
| US3330665A (en) * | 1964-03-17 | 1967-07-11 | Monsanto Co | Cold water soluble acid compositions |
| GB1143800A (ja) | 1966-06-23 | |||
| US3770390A (en) * | 1971-02-26 | 1973-11-06 | Dow Chemical Co | Crystal habit modification of inorganic salts using polymeric sulfonates or sulfates |
| GB1373167A (en) | 1972-01-26 | 1974-11-06 | Ici Ltd | Manufacture of dyestuff powder |
| US4254283A (en) * | 1979-06-07 | 1981-03-03 | Monsanto Company | Process for preparing adipic acid with recovery of glutaric and succinic acids |
| JPS60169436A (ja) * | 1984-02-14 | 1985-09-02 | Nippon Shokubai Kagaku Kogyo Co Ltd | 速溶性フマ−ル酸組成物 |
| DE3434918A1 (de) * | 1984-09-22 | 1986-04-03 | Hüls AG, 4370 Marl | Verfahren zur gewinnung von l-aepfelsaeure |
| US5034105A (en) * | 1989-07-27 | 1991-07-23 | Michigan Biotechnology Institute | Carboxylic acid purification and crystallization process |
| US5104492A (en) * | 1990-07-11 | 1992-04-14 | The Regents Of The University Of California | Recovery of carboxylic acids from water by precipitation from organic solutions |
-
1997
- 1997-02-12 DE DE19705329A patent/DE19705329A1/de not_active Withdrawn
-
1998
- 1998-02-09 WO PCT/EP1998/000703 patent/WO1998035929A1/de active IP Right Grant
- 1998-02-09 US US09/367,233 patent/US6534680B1/en not_active Expired - Lifetime
- 1998-02-09 CA CA002280592A patent/CA2280592A1/en not_active Abandoned
- 1998-02-09 AU AU62961/98A patent/AU6296198A/en not_active Abandoned
- 1998-02-09 CN CN98804115A patent/CN1093115C/zh not_active Expired - Fee Related
- 1998-02-09 KR KR10-1999-7007230A patent/KR100509312B1/ko not_active IP Right Cessation
- 1998-02-09 JP JP53531798A patent/JP3984297B2/ja not_active Expired - Fee Related
- 1998-02-09 EP EP98906938A patent/EP0968167B1/de not_active Expired - Lifetime
- 1998-02-09 BR BR9807326-5A patent/BR9807326A/pt not_active Application Discontinuation
- 1998-02-09 RU RU99119595/04A patent/RU2195442C2/ru not_active IP Right Cessation
- 1998-02-09 DE DE59805697T patent/DE59805697D1/de not_active Expired - Lifetime
- 1998-02-09 PL PL98335023A patent/PL189983B1/pl not_active IP Right Cessation
- 1998-09-02 UA UA99095051A patent/UA54494C2/uk unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883640A (en) * | 1972-01-26 | 1975-05-13 | Ici Ltd | Sodium percarbonate crystals |
| US5296639A (en) * | 1992-12-18 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Adipic acid purification |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2280592A1 (en) | 1998-08-20 |
| US6534680B1 (en) | 2003-03-18 |
| KR20000070964A (ko) | 2000-11-25 |
| PL189983B1 (pl) | 2005-10-31 |
| EP0968167B1 (de) | 2002-09-25 |
| PL335023A1 (en) | 2000-03-27 |
| KR100509312B1 (ko) | 2005-08-22 |
| CN1252048A (zh) | 2000-05-03 |
| BR9807326A (pt) | 2000-04-18 |
| RU2195442C2 (ru) | 2002-12-27 |
| WO1998035929A1 (de) | 1998-08-20 |
| UA54494C2 (uk) | 2003-03-17 |
| DE19705329A1 (de) | 1998-08-13 |
| JP3984297B2 (ja) | 2007-10-03 |
| AU6296198A (en) | 1998-09-08 |
| JP2001511791A (ja) | 2001-08-14 |
| DE59805697D1 (de) | 2002-10-31 |
| EP0968167A1 (de) | 2000-01-05 |
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